[2] Calderón got his big break in 1984 in a revival of Miguel Piñero's Short Eyes directed by Kevin Conway at the Second Stage Theatre.
He wrote and directed Master of the Crossroads, based on his own short story; it was premiered at the Bridge Theater in Manhattan, starring Kate Jackson.
[4] Calderón was almost cast as Jules Winnfield in the 1994 film Pulp Fiction, since director Quentin Tarantino had been impressed by his audition, but the role eventually went to Samuel L. Jackson, and Calderón was given a role as a bartender, Paul,[5] who speaks the line, "Hey, my name's Paul and this shit's between y'all," to John Travolta's character, Vincent Vega.
[6] He has performed in numerous feature films, including King of New York, Sea of Love, The Last Castle, The Firm, Four Rooms, Out of Sight, La Soga, Cop Land, Addiction, and 21 Grams.
He has made many guest appearances on television series, including recurring roles on Dream Street, Law & Order and Miami Vice.
In 2014, he played Arquimedes, the bodyguard of Enoch "Nucky" Thompson in seven episodes of the fifth (final) season of the HBO series Boardwalk Empire.